At the end of the film where Nick shoots his brother Conrad who then plays possum at the roof, how'd Conrad manage to reach the gala hall during Nick's jump?
It probably took a few minutes for the paramedics to check Nicholas over after his landing, and the time is justifiably compressed because he's so disoriented. Not long, but long enough for Conrad to stop playing possum and rush down via express elevator.
If the gunshots were all blanks and squibs, then how the tire on the (fake) private investigator's car get blown out by the gunshot? They would have had to known in advance that (a)Nicholas Van Orton would have confronted the private investigator (b)he would have stolen the gun (c)he would have shot the gun and (d)he would have shot it at the tire.
They could've just guessed he might do that. The PI could've been wearing a squib shirt too. The point is, it was entirely optional. It wasn't necessary to that scene that he take the gun and shoot anything, just that he think someone had sent a PI after him.
Indeed, they probably had all four tires rigged to blow if necessary, and probably set up all the windows and side mirrors to break on cue as well. If he'd shot at part of the car that wasn't pre-rigged, like the body of the vehicle, they'd blow the nearest squib to where he was aiming and pretend he'd just missed his exact target.
Perhaps the gun was loaded with live rounds. They would not have expected Van Orton to actually shoot someone, and he didn't.
If the gunshots were all blanks and squibs, then how did the car window get bullet holes in it?
You answered your own question, blanks are what makes the muzzle flash from the gun, and squibs are the bullet "hits". They likely used the exact same method as a movie shoot would.
Hole-punching squibs are rarely used in movie-shoots, the shot panel is filmed in a cut-away scene. Using real squibs in a scene where there are people risk injury as the "shooting" will create shrapnel. That ignored the fact that to do so on a see-through object like a car window wouldn't work, the squibs would be visible.
How did they know what part of the building he would jump from?
It's a bit of a stretch, but Feingold mentions that if he hadn't jumped at all, he was supposed to throw him off. If Nick had wandered toward the wrong part of the roof in a suicidal daze — and they had enough of his actions planned already — he probably could have caught him and gotten him back on the rails.
On a related note, what if he'd not bothered to jump and shot himself on the spot instead? Even a blank can kill if it's fired with the gun's muzzle set directly against the skull.
Indeed. This movie is full of plot-holes that are just handwaved away, but the ending is nothing but a long series of them. Nicholas shoots his brother with blanks, and it's just taken on faith that he will not check that the gun is properly loaded. After apparently killing Conrad, he doesn't shoot himself, but instead jumps off of a random, but the exact right, spot, misses the, visible on camera, I-beams holding the class ceiling by a few feet, and lands perfectly safe on an air mattress after an uncontrolled multi-floor fall. Any one of these events could have gone uncontrollably wrong and cause massive injury if not death
How many "games" does CRS put on at one time? Do all the employees focus just on Nick or are there a lot of these going on at various spots in the city?
Given the insane amount of prep-work and number of people involved in just Nick's game, it's likely that they only put on, at most, one or two Games a month, and no more than one a year would take place in the same city. There might be CRS 'scriptwriters' who plan out the next scenario while a given Game is still running, but staging multiple overlapping Games wouldn't make sense logistically. Not to mention, it'd be awfully hard to keep what they're doing a secret from potential future customers or the police - remember that they can only market the Game to people who don't know what to expect of one, and a lot of what happens to and around Nick (kidnapping, reckless endangerment, staged gunfights and vehicular accidents) is illegal as hell, regardless of whether or not the violence is staged - if they did these things too often.
What was there contingency plan for trapping a guy in a sinking car?
There was, when Christine is trying to calm Nicholas, she tells him that there was a diver underwater.
The Mind Experiment:
As soon as you forgot it you're playing. As soon as you think about it you lose. Loss must be announced. What happens if you break a rule?
You lose. Duh.
You seem to be forgetting the fact that the one possible option in the game is to lose it.
If you break a rule, like not announcing a loss, then you "cheated", which is worse than losing, morally speaking.
Not if you interpret it as just not ruining the game for everyone around you.
The rule is, you have to announce it. If you do, it doesn't count as a loss for the people you announce it to. If you don't, there's no real consequences, but you'll know you cheated.
Of course everyone you announce it to loses, As soon as you mention the Game to anyone who knows about it, they lose. And I lost when I saw the Head Line for the Headscratcher too.
What happens is nothing. The Game defines no penalty for cheating.